Sec-Butylamine → 3-Chloro-N-(1-methylpropyl)-2,4-dinitro-6-(trifluoromethyl)benzenamine

HRID 1658947Notes

Reaction equation

HRID 1658947 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[CH:19]([NH2:23])([CH2:21][CH3:22])[CH3:20]>C(O)C>[CH:19]([NH:23][C:2]1[C:3]([C:15]([F:18])([F:17])[F:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([Cl:11])[C:7]=1[N+:8]([O-:10])=[O:9])([CH2:21][CH3:22])[CH3:20]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 214130983-Chloro-N-(1-methylpropyl)-2,4-dinitro-6-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 20 g. (0.0655 mole) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 150 ml. of absolute ethanol was added 9.58 g. (0.131 mole) of sec-butylamine, dropwise, over a period of about 15 minutes. The resultant solution was refluxed for two hours and the ethanol then removed by distillation under reduced pressure. The solid yellow residue was triturated with 300 ml. water to dissolve the sec-butylamine hydrochloride. The water insoluble product was isolated by filtration, washed with water, and then dissolved in 600 ml. of refluxing 95% ethanol. Upon cooling, the product crystallized. Filtration gave 20.4 g. of a yellow crystalline solid, melting at 90.5° - 91.5°C.

Workup

  1. additionTo a stirred mixture of 20 g
  2. customthe ethanol then removed by distillation under reduced pressure
  3. customThe solid yellow residue was triturated with 300 ml
  4. dissolutionwater to dissolve the sec-butylamine hydrochloride
  5. customThe water insoluble product was isolated by filtration
  6. washwashed with water
  7. dissolutiondissolved in 600 ml
  8. temperatureof refluxing 95% ethanol
  9. temperatureUpon cooling
  10. customthe product crystallized
  11. filtrationFiltration
  12. customgave 20.4 g

Sources & evidence

ORD record
ord-413a1681bb004f1a9fd2c7458fb1b079
Source dataset
uspto-grants-1976_06
Patent number
US03966816

Reaction notes

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